Chlorosulfonic acid → HCID 20201772, compound

HRID 979202Notes

Reaction equation

[C:1]([C:4]1[O:5][C:6]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:7]=2[CH:8]=1)(=[O:3])[CH3:2].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[C:1]([C:4]1[O:5][C:6]2[C:12]([S:16]([Cl:15])(=[O:18])=[O:17])=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[C:7]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 3042306Ethanone, 1-(4-methoxy-2-benzofuranyl)-

Product 1

HCID 20201772HCID 20201772, compoundYield 93%

Procedure

There was reacted 0.95 g (5 mmole) of 2-acetyl-4-methoxybenzofuran with chlorosulfonic acid as in Example 1, yielding 1.3 g of 2-acetyl-4-methoxy-7-chlorosulfonylbenzofuran (yield: 93%, MS (m/z): 288 (M+), 273, 253 and 189). The obtained chlorosulfonyl compound was reacted with glycine ethyl ester hydrochloride to give an ester compound (yield: 97%, MS (m/z): 354 (M+), 281, 252 and 188), which was then hydrolyzed to give 2-acetyl-4-methoxy-7-(N-carboxymethylsulfamoyl)benzofuran (yellow plates, yield: 84%). The physical constants are shown in Table 4.

Sources & evidence

ORD record: ord-40fa22f6815d479aac43c3277504dc60
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04666931

Reaction notes

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